6336-07-8

Usage

InChI:InChI=1/C17H16O4/c1-19-12-5-3-11(4-6-12)17-10-15(18)14-9-13(20-2)7-8-16(14)21-17/h3-9,17H,10H2,1-2H3

Upstream product

• 114021-51-1 (2E)-1-(2-hydroxy-5-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 54401-48-8 C₁₇H₁₆O₄ 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 54401-47-7 6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 114021-51-1 (2E)-1-(2-hydroxy-5-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Enzyme-assisted cyclization of chalcones to flavanones

Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.

Synthetic analogs of natural flavolignans. XV. Isomerization of 2′-hydroxychalcones into flavanones using triethylamine

A simple and effective method for preparing synthetic analogs of natural flavanones via isomerization of 2′-hydroxychalcones with triethylamine was proposed.